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My boss (not a tech writer, though he did play one on TV for a while) would
like to change the alignment of text in tables in our documents. He wants to
center text vertically, particularly in tables where one column has more
text than others (and cells with less text have lots of empty, white space).

His argument is that, with top-aligned text, the text in the left column
seems to apply only to the first line of text in the right column, but, if
the text in the left column is centered vertically, it more clearly applies
to all the text in the right column.

To me, it is just the opposite. Text in the left column should be aligned
with the beginning of text it applies to in the right column. Additionally,
top alignment of text in tables seems to be the norm. I can't find even one
publication with text centered vertically in tables. But my boss is
insistent; he really wants this change. He challenged me to persuade him he
is wrong by maybe bringing in some books that say you should always top
align text. But he also said that even then he might not be persuaded.

I thought maybe Edward Tufte addresses alignment of text in tables in one of
his books? But is this battle even worth fighting? My sense is that, at the
least, since readers are accustomed to top alignment, they will have to do a
double-take if we use a vertical center alignment. I don't want that, but
neither do I want to get petty over layout, especially with a boss who's a
nice guy and generally agreeable to my recommendations.